Chris Stapleton is undoubtedly one of the most popular country artists of the 21st century. With his bluesy twang, awesome guitar skills and humble persona, it’s not hard to see why Stapleton has earned multiple awards for his work. And the music isn’t the only thing memorable about the Tennessee Whisky singer.
Stapleton’s fashion sense also makes him stand out and adds to his ramblin’ man mystique, just like Riley Green’s and Luke Combs’ clothing have become an iconic part of their presentations. So, if you’re Googling ‘What does Chris Stapleton wear?’ or ‘How can I dress like Chris Stapleton?’ you’re in the right place.
This edition of Country Fit Check will tell you everything you need to know about how to achieve the Chris Stapleton look.
Shirts and jackets
Stapleton is known for his rustic and utilitarian style that combines vintage Americana, flannel and workwear. One of his favourite brands is Filson because of its functionality and comfort, which he was introduced to by his dad. Stapleton confirmed this in an interview with Filson:
“I was introduced to Filson by my dad. He used your products to go hunt – he was a bird hunter and he kept English setters, trained them and hunt grouse, quail, and pheasant. Anytime he had some free time in different parts of the United States, he’d go hunting and he always had something Filson with him in the process.”
It’s no surprise then that Stapleton has collaborated with the brand in both clothing and travel supplies, including backpacks and travel bags.
Beyond this collaboration, Stapleton is often dressed in either flannel or Western-style yoke shirts. The recommendations below are a reflection of his practical style:
Image credit: Filson.
Chris Stapleton signature Mackinaw cruiser
In partnership with Filson, Stapleton helped to revive an iconic product from the range. The creation of this cruiser stemmed from his discovery of a vintage plaid cruiser in the Filson archive. While it was faded and covered in patina, the jacket had held up for fifty years, and that spoke to the singer’s appreciation for heritage.
The cruiser is designed to hold up in unpredictable weather and is made from durable cotton with tight weave. This makes it highly durable and breathable, and ideal for wearing in the outdoors.
Fair warning. It’s a pricy jacket, albeit one that has been made with a genuine sense of collaboration, like everything Stapleton does.
Another Filson and Stapleton collaboration, the state of kind t-shirt was created to support the singer’s charity that provides aid for natural disaster relief. It comes in peat black and is made from cotton.
Ralph Lauren slub denim western shirt
Stetson embroidered black denim shirt
Ariat straight shooter t-shirt
Buffalo plaid pearl snap flannel
Jeans
Wrangler 13MWZ Original cowboy cut jeans
Ariat M4 Coltrane bootcut jeans
Image credit: Chris Stapleton’s cowboy hat replica made by Wild Hats. Appeared on Instagram @wildhatsofficial
Hats
Perhaps the most iconic part of Stapleton’s look is his signature cowboy hat that has been with him on the road for many years. In fact, his hat has been nicknamed ‘Precious’ by Stapleton’s crew. His hat appears to be a Charlie 1 Horse Hat with a snakeskin band embellished with bird feathers and a notable turquoise stone.
Chris Stapleton hat recommendations
Charlie 1 Horse country with a flare western hat
Stetson Skyline 7242 6x cowboy hat
Boots
As far as cowboy boots go, Stapleton is a huge fan and collector of Lucchese boots. In an interview with Esquire, he said:
“The first pair of Luccheses that I owned [the Lucchese team] built for me…But, you know, they were kind enough to give me a tour of the factory. I was on a radio tour. I wasn’t anybody, really. But, they offered me a pair of boots. And I said, “You know, I just want something I can wear every day.”
Image credit: Lucchese.
I mishmashed some different features they had in the room—they had this really nice room, you know like a Charlie and the Chocolate Factory, Willy Wonka room for boots, and that became the first pair of Luccheses that I owned. I owned some other boots, I’d tried on some Luccheses, but hadn’t taken the dive yet. And when they built me that pair it was over. That’s only brand of cowboy boots I’ve worn since.”
Of course he ended up collaborating with Lucchese on his own collection, products that are extremely hard to get your hands on these days. But the recommendations here still fit with Stapleton’s appreciation for fine detail and hardwearing boots.
Chris Stapleton cowboy boots recommendations
Tony Lama Plano 12 Suede boots
Style yourself with these other Country Fit Check guides
The beautiful thing about country is that it’s an increasingly fluid genre reflected in the music and fashion. Artists have developed their own style, brand collaborations and accessories and here are some other Country Fit Check guides for you:
Country Fit Check: The Morgan Wallen edition
Americana Aspects 
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